Total synthesis of 11-deoxydaunomycinone and analogs by a tandem Claisen-Diels-Alder strategy

dc.contributor.author Kraus, George
dc.contributor.author Woo, Soon Hyung
dc.contributor.author Kraus, George
dc.contributor.department Chemistry
dc.date 2018-02-17T09:06:35.000
dc.date.accessioned 2020-06-30T01:21:59Z
dc.date.available 2020-06-30T01:21:59Z
dc.date.copyright Thu Jan 01 00:00:00 UTC 1987
dc.date.issued 1987-10-01
dc.description.abstract <p>11-Deoxydaunomycinone (6), ita 4-deoxy analogue 5, and 1-methoxy-4,ll-dideoxyduanomycinone were prepared by a sequence involving an intramolecular acyl transfer reaction followed by a tandem Claisen-Diels-Alder reaction. The resulting diketone could be oxidized to naphthoquinone 11 with DDQ. This quinone was then treated with either 1-[ (trimethylsilyl)oxy]butadiene or l-methoxy-1,3-cyclohexadiene to provide adducts that could be transformed into 5 and 6. Unfortunately, the presence of the C-7 carbonyl group decreased the regioselectivity of 11 in Diels-Alder reactions.</p>
dc.description.comments <p>Reprinted (adapted) with permission from <em>The Journal of Organic Chemistry,</em>52(22); 4841-4846. Doi: <a href="http://dx.doi.org/10.1021/jo00231a003" target="_blank">10.1021/jo00231a003</a>. Copyright 1987 American Chemical Society.</p>
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dc.identifier archive/lib.dr.iastate.edu/chem_pubs/677/
dc.identifier.articleid 1680
dc.identifier.contextkey 7954385
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/677
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/15158
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/677/0-1987_KrausGA_ACS_License_TotalSynthesis11Deoxy.pdf|||Sat Jan 15 01:28:04 UTC 2022
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/677/1987_KrausGA_TotalSynthesis11Deoxy.pdf|||Sat Jan 15 01:28:05 UTC 2022
dc.source.uri 10.1021/jo00231a003
dc.subject.disciplines Chemistry
dc.subject.disciplines Environmental Chemistry
dc.subject.disciplines Inorganic Chemistry
dc.subject.disciplines Organic Chemistry
dc.subject.disciplines Other Chemistry
dc.subject.disciplines Polymer Chemistry
dc.title Total synthesis of 11-deoxydaunomycinone and analogs by a tandem Claisen-Diels-Alder strategy
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication 773dd84a-1494-40ee-aebf-549f26a04a22
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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